3 insights into the future of business from Steven Bartlett

Hello and welcome to Modern CEO! I’m Stephanie Mehta, CEO and chief content officer of Mansueto Ventures. Each week this newsletter explores inclusive approaches to leadership drawn from conversations with executives and entrepreneurs, and from the pages of Inc. and Fast Company. If you received this newsletter from a friend, you can sign up to get it yourself every Monday morning. 

If you want a glimpse of the future of business, I recommend spending a few hours with Steven Bartlett, entrepreneur, investor, and host of the The Diary of a CEO podcast. 

I did just that earlier this month, when I interviewed Bartlett alongside PwC partners at a series of Daily Decode sessions the professional services firm hosted at South by Southwest (SXSW). Bartlett’s observations and experiences are worth clocking because he is, in many ways, a leading indicator of where business is going: He is an AI power user and promotes its widespread use at the companies he’s founded. He’s young (33 years old), and he’s influencing a new generation of leaders: The Diary of a CEO was Spotify’s No. 1 business and tech podcast last year. 

Here are three insights that stood out from my conversations with Bartlett: 

1. He’s hiring “agent maxxers.” Bartlett says that as more labor can be handled by AI agents—software that can autonomously perform tasks—he sees work at his companies increasingly shifting to specialists, such as a chief financial officer with irreplaceable domain and company knowledge who can direct an agent to supplement their job. He calls these people “agent maxxers”—those who truly understand the technology. “I’m not [hiring] anyone in between,” he says, noting that he recently spoke with a promising candidate who said she’d not used Claude Code—nor had she built anything with agents. She didn’t get the job.

2. Obvious pain paralysis is the new Innovator’s Dilemma. Bartlett suggests that many companies have “obvious pain paralysis”—a tendency to try to address or lessen the pain in front of them, deferring decisions when the upside is vague and distant. He points to return-to-office policies as an example: Leaders didn’t bring folks back to the office for fear that people would quit and because management couldn’t articulate or quantify the benefits. He says he sees the same thing happening with AI and urges executives to think expansively about the possibilities: “In moments of great transition, you have to take bold, decisive action and make difficult decisions now or [face] more difficult decisions later,” he says. “We’re all in that position, including me.”

Bartlett’s assessment feels like a 2026 take on Clayton Christensen’s Innovator’s Dilemma, which chronicled how successful companies failed because they focused on addressing the issues of today while failing to foresee new technologies that would make them obsolete. The lesson of both: disrupt before you get disrupted.

3. He’s creating a culture of “pushing on paper walls.” One way Bartlett makes sure that his companies stay nimble (and perhaps avoid disruption) is to institutionalize challenging the status quo. He calls this “pushing on paper walls” or questioning whether a constraint, or wall, is real or flimsy like paper. If a vendor says a project will take six weeks, Bartlett’s team is encouraged to ask for a tighter turnaround; internal processes are constantly evaluated to see if they can be done quicker or smarter. His companies use their communications channels to celebrate the dismantling of paper walls. “When you open up Slack, and you see the intern or the CFO going, ‘I found a paper wall today,’ [you] can imagine what that breeds in an organization in terms of culture,” he says. 

From his perch as an entrepreneur, creator, and millennial, Bartlett certainly has the flexibility to experiment and provide a window into the future of business. But his worldview—a landscape that’s AI-centric, fast-moving, and disruptive—isn’t radical. It’s the new normal. 

How are you preparing for what’s next?

How are you future-proofing your company? Do you have a version of “agent maxxers” or “paper walls” that you celebrate? Send your ideas to me at stephaniemehta@mansueto.com. I’ll publish the best examples in a future newsletter. 

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